CN103113336A - Aurone compound as well as preparation method and application thereof - Google Patents
Aurone compound as well as preparation method and application thereof Download PDFInfo
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- CN103113336A CN103113336A CN2013100379009A CN201310037900A CN103113336A CN 103113336 A CN103113336 A CN 103113336A CN 2013100379009 A CN2013100379009 A CN 2013100379009A CN 201310037900 A CN201310037900 A CN 201310037900A CN 103113336 A CN103113336 A CN 103113336A
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Abstract
The invention discloses an aurone compound as well as a preparation method and application thereof. The aurone compound is extracted from rose, the 4' site and the 6 site of the aurone compound are methoxyl, wherein the 4' site and the 6 site are shown in formula of the description, and named as 5-hydroxyl-6,4'-methoxyaurone. The preparation method for the aurone compound comprises the following steps of: treating materials, ultrasonically extracting the materials, carrying out column chromatography on silica gel, carrying high-pressure liquid phase chromatographic separation and carrying out gel column chromatography. The invention further discloses the application of the aurone compound in preparing tobacco mosaic virus. The aurone compound disclosed by the invention is firstly separated from the roe, and the molecular formula and the structure of the aurone compound can be confirmed. The preparation method adopts alcohol as a solvent, is little in pollution to the environment, safe and environment-friendly. The aurone compound is simple in structure and can easily achieve artificial synthesis. According to the test adopting a half-leaf method, the relative inhibition ratio of the compound to the tobacco mosaic virus is 22.2%, which is nearly 28.9% of the inhibition ratio of the contrast ningnanmycin, and the IC50 value is 62.5 microns. Besides, the aurone compound can be used as a guiding compound of a drug for preventing tobacco mosaic virus.
Description
Technical field
The invention belongs to effective ingredients in plant extractive technique field, be specifically related to a kind of aurones compounds and preparation method thereof and application.
Background technology
Gul is one of most important ornamental plant monoid in the world.Some kind of rose such as Chinese rose, prominent fern rose and moss rose are famous ornamental flower and spice berry, because it can in order to extract rose oil or as ornamental flower, to possess higher commercial value, now extensively be planted in a plurality of areas in Yunnan Province.Simultaneously, its petal and bud also can be used as food, or are used for the treatment of stomachache, diarrhoea and gynaecopathia as medicine, and studies show that Weibull, flavonoid and the terpene of plant chemical ingredient in the past are the main chemical compositions of separating from gul.Flavones is the biologically active substance that a class occurring in nature extensively exists, and because flavone component structure type in plant is many, stereochemistry is complicated, has multiple biological activity, and is very active to the research in this field both at home and abroad; Aurones belongs to rare flavonoid compound, due to its significant biological activity, no matter is naturally occurring, or the aurones compounds that obtains of synthetic, has all caused chemist's extensive concern.Therefore, in the further investigation gul, the type of aurones, have more far reaching significance to the utility value that promotes gul.
Summary of the invention
The first purpose of the present invention is to provide a kind of aurones compounds; The second purpose is to provide the preparation method of this compound; The 3rd purpose is to provide the application of this compound in preparation resisting tobacco mosaic virus medicine.
The first purpose of the present invention is achieved in that described aurones compounds separates and obtains from Rose, its molecular formula is C
17H
14O
5, structural formula is:
This compound called after: 5-hydroxyl-6,4 '-the methoxyl group aurones (5-hydroxy-6,4 '-methoxyaurone).
The second purpose of the present invention is achieved in that described aurones compounds preparation method comprises that raw material processing, supersound extraction, silica gel column chromatography, high pressure liquid chromatography are separated, gel filtration chromatography, is specially:
A, raw material are processed: get the raw material Rose, 20 ~ 40 mesh sieves are crossed in coarse reduction;
B, supersound extraction: the ethanol take 60 ~ 80% is solvent, supersound extraction 2 ~ 4 times, and each 4 ~ 8h merges extracting solution, filter, and concentrating under reduced pressure becomes medicinal extract;
C, silica gel column chromatography: with the pure dissolve with methanol of medicinal extract with 1.5 ~ 3 times of amounts of weight ratio, with upper silicagel column after the 80-100 order silica gel mixed sample of 1 ~ 3 times of medicinal extract weight, chloroform-methanol solution gradient washing take volume proportion as 20:1 ~ 10:10, collect respectively the elutriant of each several part and concentrate, merging identical part with the TLC monitoring;
D, high pressure liquid chromatography separate: get the elutriant of volume proportion 9:1 part, the methyl alcohol take 45 ~ 50% is moving phase, take specification as 21.2mm * 250mm, the C of 7 μ m
18Preparative column is stationary phase, and flow velocity is 12ml/min, and it is 254nm that UV-detector detects wavelength, and each sample introduction 200 μ L collect the chromatographic peak of 35.8min, repeatedly cumulative after evaporate to dryness, obtain the crude product of the compounds of this invention;
E, gel filtration chromatography: upper Sephadex LH-20 gel column after the pure dissolve with methanol of 1 ~ 2 times of amount of crude product use weight ratio, carry out wash-out with pure methyl alcohol, sub-bottle is collected, and the 0.8-0.9 L partial concentration of wash-out effluent liquid is described aurones compounds.
Structure with the aurones compounds of aforesaid method preparation is to measure out by the following method:
The compounds of this invention is yellow jelly, UV spectrum (solvent is methyl alcohol), and UV (MeOH),
l max(log
e) 370 (3.92), 309 (3.68), 250 (3.56), 230 (4.18) nm; Infrared spectra (pressing potassium bromide troche)
max3354,2962,2907,1679,1615,1542,1482,1262,1148,1056,876,753 cm
-1High resolution mass spectrum provides quasi-molecular ion peak
m/z[321.0733 M+Na]
+(C
17H
14NaO
5Calculated value 321.0739).In conjunction with
1H and
13C NMR spectrum provides a molecular formula C
17H
14O
5, degree of unsaturation is 11.
Compound
1H and
13C NMR data (in Table 1) show in compound 17 carbon signals and 14 hydrogen signals, comprise 1 aromatic rings signal [C-4 (
δ C105.2 d), C-5 (
δ C145.8 s), C-6 (
δ C148.7 s), C-7 (
δ C101.0 d), C-8 (
δ C156.3 s), C-9 (
δ C126.0 s)] and with 2 fragrant proton signals [H-4 (
δ H7.15 s) and H-7 (
δ H6.82 s)]; Another 1 aromatic rings signal [C-1 ' (
δ C123.5 s), C-2 ', 6 ' (
δ C130.9 d), C-3 ', 5 ' (
δ C117.2), C-4 ' (
δ C160.0 s)] and with 4 fragrant proton signals [H-2 ', 6 ' (
δ H7.76, d,
J=8.6) and H-3 ', 5 ' (
δ H6.99, d,
J=8.6)], 1 carbonyl carbon signal (C-10,
δ C186.5 s), the 1 pair of carbon-carbon double bond signal [C-2 (
δ C152.0 s) and C-3 (
δ C118.9 d); H-3 (
δ H7.58 s)], 2 methoxyl group signals (
δ C55.9 and 56.0;
δ H3.89 and 3.82), 1 phenolic hydroxyl group signal (
δ H9.27).Infrared spectra shows hydroxyl (3354 cm
-1), carbonyl (1679 cm
-1) and aromatic ring (1615,1542,1482 cm
-1) absorption peak.UV spectrum is 370,309, and 250 and 230 places have absorption peak to confirm that also aromatic ring exists.Exist in compound H-3 (
δ H7.58, s) and C-2 (
d C152.0), C-3 (
d C118.9), C-10 (
d C186.5), H-3 (
δ H7.58) and C-2 (
δ C152.0)/C-4 (
δ C105.2)/C-8 (
δ C156.3)/C-9 (
δ C126.0)/C-10 (
δ C186.5), H-4 (
δ H7.15) and C-3 (
δ C118.9) and H-2 ', 6 ' (
δ C130.9) and C-10 (
δ C186.5) HMBC relevant confirm that also compound is the aurones class formation, and be connected with C-8 at C-2 and connect with furan nucleus.The hydrogen signal of 4 couplings in proton nmr spectra
δ H7.03 (d,
J=8.6 Hz, 2H) and 7.74 (d,
J=8.6,2H), confirm in compound the C ring be 4 '-replace; 2 unimodal
δ H(7.29 s, 1H) and
δ H6.69 (s, 1H) signal can infer that the B-ring of compound replaces for C-5/C-6.The phenolic hydroxyl group signal (
δ H9.27) and C-4 (
δ C105.2), C-5 (
δ C145.8), and C-6 (
δ C148.7) HMBC relevant confirm that phenolic hydroxyl group is substituted in the C-5 position.The methoxyl group signal (
δ H3.89 with 3.82) and C-6 (
δ C148.7)/C-4 ' (
δ C160.0) HMBC relevant confirm that methoxy substitution is in the C-6 of compound position and C-4 ' position.On the other hand, the phenolic hydroxyl group signal (
δ H9.27) (
δ H9.27) and C-4 (
δ C105.2), C-5 (
δ C145.8) and C-6 (
δ C148.7) HMBC is relevant also supports phenolic hydroxyl group in the C-5 position.On the NOESY spectrum (
δ H3.89 and 3.82) and H-7 (
δ H6.82)/H-3 ', 5 ' (
δ H6.99) relevant support methoxyl group in C-6 position and C-4 ' position.Therefore the structure of compound is determined.
Table 1 compound
1H and
13C NMR data (CD
3OD, 500 and 125 M Hz)
The 3rd purpose of the present invention is achieved in that the application of described aurones compounds in preparation resisting tobacco mosaic virus medicine.
Aurones compounds of the present invention is to separate from Chinese rose first, adopted the POP data validations such as nucleus magnetic resonance, mass spectrum, infrared spectra, UV spectrum its molecular formula and structure.Aurones compounds extracting method of the present invention is simple, and compound structure is simple, and synthetic also is easy to realize.This compound is by the activity of its resisting tobacco mosaic virus of half leaf method experimental test, result proves that this compound is 22.2% to the relative inhibition of tobacco mosaic virus (TMV), higher than 28.9% of contrast Ningnanmycin, illustrate that this compound has good activity of resisting tobacco mosaic virus, can be used as the guiding compound of activity of resisting tobacco mosaic virus.
Description of drawings
Fig. 1 is preparation method's process flow sheet of the present invention;
Fig. 2 be the compounds of this invention proton nmr spectra (
1H NMR) figure.
Fig. 3 be the compounds of this invention carbon-13 nmr spectra (
13C NMR) figure.
Fig. 4 is the main HMBC correlogram of the compounds of this invention.
Embodiment
The present invention is further illustrated below in conjunction with accompanying drawing, but never in any form the present invention is limited, and any conversion or improvement based on training centre of the present invention is done all fall into protection scope of the present invention.
Aurones compounds of the present invention separates from Rose and obtains, and its molecular formula is C
17H
14O
5, structural formula is:
This compound called after: 5-hydroxyl-6,4 '-the methoxyl group aurones (5-hydroxy-6,4 '-methoxyaurone).
Aurones compounds preparation method of the present invention comprises that raw material processing, supersound extraction, silica gel column chromatography, high pressure liquid chromatography are separated, gel filtration chromatography, is specially:
A, raw material are processed: get the raw material Rose, 20 ~ 40 mesh sieves are crossed in coarse reduction;
B, supersound extraction: the ethanol take 60 ~ 80% is solvent, supersound extraction 2 ~ 4 times, and each 4 ~ 8h merges extracting solution, filter, and concentrating under reduced pressure becomes medicinal extract;
C, silica gel column chromatography: with the pure dissolve with methanol of medicinal extract with 1.5 ~ 3 times of amounts of weight ratio, with upper silicagel column after the 80-100 order silica gel mixed sample of 1 ~ 3 times of medicinal extract weight, chloroform-methanol solution gradient washing take volume proportion as 20:1 ~ 10:10, collect respectively the elutriant of each several part and concentrate, merging identical part with the TLC monitoring;
D, high pressure liquid chromatography separate: get the elutriant of volume proportion 9:1 part, the methyl alcohol take 45 ~ 50% is moving phase, take specification as 21.2mm * 250mm, the C of 7 μ m
18Preparative column is stationary phase, and flow velocity is 12ml/min, and it is 254nm that UV-detector detects wavelength, and each sample introduction 200 μ L collect the chromatographic peak of 35.8min, repeatedly cumulative after evaporate to dryness, obtain the crude product of the compounds of this invention;
E, gel filtration chromatography: upper Sephadex LH-20 gel column after the pure dissolve with methanol of 1 ~ 2 times of amount of crude product use weight ratio, carry out wash-out with pure methyl alcohol, sub-bottle is collected, and the 0.8-0.9 L partial concentration of wash-out effluent liquid is described aurones compounds.
Described pure methyl alcohol is as eluent, and sub-bottle is collected, as calculating with every bottle of 100 mL, so the invention compound in the 8th to the 9th bottle, i.e. 0.8 ~ 0.9 L of effluent liquid.
The described alcohol concn of B step is 70%, supersound extraction 3 times, each 6h.
The described medicinal extract of C step is with the pure dissolve with methanol of 2 times of amounts of its weight ratio.
The described medicinal extract of C step is used 80 ~ 100 order silica gel mixed samples of 1 ~ 2 times of medicinal extract weight ratio after dissolve with methanol.
The described chloroform-methanol volume proportion of C step is 20:1,9:1,8:2,7:3,6:4,5:5.
The described silicagel column of C step fills posts with 200～300 order silica gel of 1 ~ 2 times of medicinal extract weight.
The described moving phase of D step is 48% methyl alcohol.
The described crude product of the E step pure dissolve with methanol of 1.5 times of amounts of weight ratio.
The application of aurones compounds of the present invention in preparation resisting tobacco mosaic virus medicine.
Aurones compounds of the present invention is to separate from Chinese Rose first, adopted the POP data validations such as nucleus magnetic resonance, mass spectrum, infrared spectra, UV spectrum its molecular formula and structure.Aurones compounds extracting method of the present invention is simple, and compound structure is simple, and synthetic also is easy to realize.High pressure liquid chromatography of the present invention can select to pacify prompt logical sequence 1,100 half preparation high pressure liquid chromatography, and the gel filtration chromatography step has adopted Sephadex LH-20 gel column, and the gel column of other types can be realized purpose of the present invention equally.
Tobacco of the present invention is raw materials used not limited by area and kind, all can realize the present invention, and the present invention will be further described with the Chinese Rose sample that derives from inhabitants of Yuxi City in Yunnan Province for the below:
China's Rose sample picks up from inhabitants of Yuxi City in Yunnan Province, and Chinese Rose sample 5.5kg is crushed to 20 orders.Sample after pulverizing is placed in 60% ethanol supersound extraction 2 times, and each 4h merges extracting solution, filter, and concentrating under reduced pressure obtains medicinal extract 260g.Add the 450 pure methyl alcohol of mL in medicinal extract, with the 80 thick silica gel mixed samples of order of 450g, then go up silicagel column, the 200 order silica gel of 800 g that pack in silicagel column after dissolving; Take volume proportion as 20:1, the chloroform-methanol mixed solvent gradient washing of 9:1,8:2,7:3,6:4,5:5, collect respectively the elutriant of each several part and concentrated, merge identical part with the TLC monitoring.Get the elutriant of volume proportion 9:1 part, the methyl alcohol take 48% is moving phase, take specification as 21.5 * 250mm, the C of 7 μ m
18Preparative column is stationary phase, and flow velocity is 18 ml/min, and it is 254nm that UV-detector detects wavelength, and each sample introduction 200 μ L collect the chromatographic peak of 35.8min, repeatedly cumulative after evaporate to dryness, obtain head product 0.96 g of the compounds of this invention.The pure methyl alcohol that adds 2.5 mL in crude product, after dissolving, upper Sephadex LH-20 gel column, use methanol-eluted fractions, and the 0.8-0.9 L partial concentration of collecting the wash-out effluent liquid namely gets sterling 0.43 g of the compounds of this invention.
Embodiment 2
China's Rose sample picks up from inhabitants of Yuxi City in Yunnan Province, and Chinese Rose sample 6kg is crushed to 40 orders.Sample after pulverizing is placed in 80% ethanol supersound extraction 4 times, and each 8h merges extracting solution, filter, and concentrating under reduced pressure obtains medicinal extract 252g.Add the 500 pure methyl alcohol of mL in medicinal extract, with the 100 thick silica gel mixed samples of order of 500 g, then go up silicagel column, the 300 order silica gel of 1000 g that pack in silicagel column after dissolving; Take volume proportion as 20:1, the chloroform-methanol mixed solvent gradient washing of 9:1,8:2,7:3,6:4,5:5, collect respectively the elutriant of each several part and concentrated, merge identical part with the TLC monitoring.Get the elutriant of volume proportion 9:1 part, the methyl alcohol take 48% is moving phase, take specification as 21.5 * 250mm, the C of 7 μ m
18Preparative column is stationary phase, and flow velocity is 18ml/min, and it is 254nm that UV-detector detects wavelength, and each sample introduction 200 μ L collect the chromatographic peak of 35.8min, repeatedly cumulative after evaporate to dryness, obtain head product 0.72 g of the compounds of this invention.The pure methyl alcohol that adds 2.5 mL in crude product, after dissolving, upper Sephadex LH-20 gel column, use methanol-eluted fractions, and the 0.8-0.9 L partial concentration of collecting the wash-out effluent liquid namely gets sterling 0.56 g of the compounds of this invention.
Embodiment 3
China's Rose sample picks up from inhabitants of Yuxi City in Yunnan Province, and Chinese Rose sample 4.5kg is crushed to 30 orders.Sample after pulverizing is placed in 70% ethanol supersound extraction 3 times, and each 6h merges extracting solution, filter, and concentrating under reduced pressure obtains medicinal extract 185g.Add the 370 pure methyl alcohol of mL in medicinal extract, with the 90 thick silica gel mixed samples of order of 350 g, then go up silicagel column, the 250 order silica gel of 600 g that pack in silicagel column after dissolving; Take volume proportion as 20:1, the chloroform-methanol mixed solvent gradient washing of 9:1,8:2,7:3,6:4,5:5, collect respectively the elutriant of each several part and concentrated, merge identical part with the TLC monitoring.Get the elutriant of volume proportion 9:1 part, the methyl alcohol take 48% is moving phase, take specification as 21.5mm * 250mm, the C of 7 μ m
18Preparative column is stationary phase, and flow velocity is 18ml/min, and it is 254nm that UV-detector detects wavelength, and each sample introduction 200 μ L collect the chromatographic peak of 35.8min, repeatedly cumulative after evaporate to dryness, obtain head product 0.66 g of the compounds of this invention.The pure methyl alcohol that adds 2.2 mL in crude product, after dissolving, upper Sephadex LH-20 gel column, use methanol-eluted fractions, and the 0.8-0.9 L partial concentration of collecting the wash-out effluent liquid namely gets sterling 0.52 g of the compounds of this invention.
The aurones compounds of getting embodiment 3 preparations carries out mass spectrum, infrared spectra, ultraviolet spectral analysis and nuclear-magnetism and detects, and result is: this compound is yellow jelly, UV spectrum (solvent is methyl alcohol), and UV (MeOH),
l max(log
e) 370 (3.92), 309 (3.68), 250 (3.56), 230 (4.18) nm; Infrared spectra (pressing potassium bromide troche)
max3354,2962,2907,1679,1615,1542,1482,1262,1148,1056,876,753 cm
-1High resolution mass spectrum provides quasi-molecular ion peak
m/z[321.0733 M+Na]
+(C
17H
14NaO
5Calculated value 321.0739).In conjunction with
1H and
13C NMR spectrum provides a molecular formula C
17H
14O
5, degree of unsaturation is 11.
Compound
1H and
13C NMR data (in Table 1) show in compound 17 carbon signals and 14 hydrogen signals, comprise 1 aromatic rings signal [C-4 (
δ C105.2 d), C-5 (
δ C145.8 s), C-6 (
δ C148.7 s), C-7 (
δ C101.0 d), C-8 (
δ C156.3 s), C-9 (
δ C126.0 s)] and with 2 fragrant proton signals [H-4 (
δ H7.15 s) and H-7 (
δ H6.82 s)]; Another 1 aromatic rings signal [C-1 ' (
δ C123.5 s), C-2 ', 6 ' (
δ C130.9 d), C-3 ', 5 ' (
δ C117.2), C-4 ' (
δ C160.0 s)] and with 4 fragrant proton signals [H-2 ', 6 ' (
δ H7.76, d,
J=8.6) and H-3 ', 5 ' (
δ H6.99, d,
J=8.6)], 1 carbonyl carbon signal (C-10,
δ C186.5 s), the 1 pair of carbon-carbon double bond signal [C-2 (
δ C152.0 s) and C-3 (
δ C118.9 d); H-3 (
δ H7.58 s)], 2 methoxyl group signals (
δ C55.9 and 56.0;
δ H3.89 and 3.82), 1 phenolic hydroxyl group signal (
δ H9.27).Infrared spectra shows hydroxyl (3354 cm
-1), carbonyl (1679 cm
-1) and aromatic ring (1615,1542,1482 cm
-1) absorption peak.UV spectrum is 370,309, and 250 and 230 places have absorption peak to confirm that also aromatic ring exists.Exist in compound H-3 (
δ H7.58, s) and C-2 (
d C152.0), C-3 (
d C118.9), C-10 (
d C186.5), H-3 (
δ H7.58) and C-2 (
δ C152.0)/C-4 (
δ C105.2)/C-8 (
δ C156.3)/C-9 (
δ C126.0)/C-10 (
δ C186.5), H-4 (
δ H7.15) and C-3 (
δ C118.9) and H-2 ', 6 ' (
δ C130.9) and C-10 (
δ C186.5) HMBC relevant confirm that also compound is the aurones class formation, and be connected with C-8 at C-2 and connect with furan nucleus.The hydrogen signal of 4 couplings in proton nmr spectra
δ H7.03 (d,
J=8.6 Hz, 2H) and 7.74 (d,
J=8.6,2H), confirm in compound the C ring be 4 '-replace; 2 unimodal
δ H(7.29 s, 1H) and
δ H6.69 (s, 1H) signal can infer that the B-ring of compound replaces for C-5/C-6.The phenolic hydroxyl group signal (
δ H9.27) and C-4 (
δ C105.2), C-5 (
δ C145.8), and C-6 (
δ C148.7) HMBC relevant confirm that phenolic hydroxyl group is substituted in the C-5 position.The methoxyl group signal (
δ H3.89 with 3.82) and C-6 (
δ C148.7)/C-4 ' (
δ C160.0) HMBC relevant confirm that methoxy substitution is in the C-6 of compound position and C-4 ' position.On the other hand, the phenolic hydroxyl group signal (
δ H9.27) (
δ H9.27) and C-4 (
δ C105.2), C-5 (
δ C145.8) and C-6 (
δ C148.7) HMBC is relevant also supports phenolic hydroxyl group in the C-5 position.On the NOESY spectrum (
δ H3.89 and 3.82) and H-7 (
δ H6.82)/H-3 ', 5 ' (
δ H6.99) relevant support methoxyl group in C-6 position and C-4 ' position.Therefore the structure of compound is determined.
The aurones compounds of getting embodiment 1,2 preparations detect according to the method for embodiment 4, have obtained identical structure.
Embodiment 6
Take the aurones compounds of embodiment 3 preparation as raw material, adopt half leaf method to carry out activity of resisting tobacco mosaic virus and detect.
When the mass concentration of medicament is 50 μ g/L, the compounds of this invention being carried out activity of resisting tobacco mosaic virus measures.5 ~ 6 age flue-cured tobacco plant on, (leaf is capable normal to choose the blade that is applicable to test, anosis without worm), first blade is evenly sprinkled fine emery powder, with writing brush with standby tobacco mosaic virus (TMV) source (on 3.0 * 10-3) blades that evenly are put on sprinkled with silicon carbide, after the blade that selects in all connects the poison end, be placed on immediately in the culture dish that fills liquid and process 20min, take out, spill on the defoliation sheet globule and about liquid, two and half leaves are restored be emitted on the enamel son of an influential official that is covered with the toilet paper moisturizing and add cover glass, temperature control (23 ± 2) ℃, be placed on the greenhouse natural light irradiation, 2 ~ 3d is visible withered spot.Each is processed and to establish second half leaf and be contrast, be provided with in addition 1 group be the commodity Ningnanmycin processing as a comparison, press formula and calculate relative inhibition:
XI%=（CK-T）/CK×100%
Wherein:
X is relative inhibition (%);
CK is soaked in the withered spot number (individual) that half sheet in clear water connects malicious leaf;
T is soaked in the withered spot number (individual) that half sheet in liquid connects malicious leaf.
Result shows: the relative inhibition of this compound is 22.2%, approaches the relative inhibition 28.9% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (10)
1. aurones compounds is characterized in that described compound separates to obtain that its molecular formula is C from Rose
17H
14O
5, structural formula is:
This compound called after 5-hydroxyl-6,4 '-the methoxyl group aurones (5-hydroxy-6,4 '-methoxyaurone).
2. an aurones compounds preparation method claimed in claim 1, is characterized in that comprising that raw material processing, supersound extraction, silica gel column chromatography, high pressure liquid chromatography are separated, gel filtration chromatography, specifically comprises:
A, raw material are processed: get the raw material Rose, 20 ~ 40 mesh sieves are crossed in coarse reduction;
B, supersound extraction: the ethanol take 60 ~ 80% is solvent, supersound extraction 2 ~ 4 times, and each 4 ~ 8h merges extracting solution, filter, and concentrating under reduced pressure becomes medicinal extract;
C, silica gel column chromatography: with the pure dissolve with methanol of medicinal extract with 1.5 ~ 3 times of amounts of weight ratio, with upper silicagel column after the 80-100 order silica gel mixed sample of 1 ~ 3 times of medicinal extract weight ratio, chloroform-methanol solution gradient washing take volume proportion as 20:1 ~ 10:10, collect respectively the elutriant of each several part and concentrate, merging identical part with the TLC monitoring;
D, high pressure liquid chromatography separate: get the elutriant of volume proportion 9:1 part, the methyl alcohol take 45 ~ 50% is moving phase, take specification as 21.2mm * 250mm, the C of 7 μ m
18Preparative column is stationary phase, and flow velocity is 12ml/min, and it is 254nm that UV-detector detects wavelength, and each sample introduction 200 μ L collect the chromatographic peak of 35.8min, repeatedly cumulative after evaporate to dryness, obtain the crude product of the compounds of this invention;
E, gel filtration chromatography: upper Sephadex LH-20 gel column after the pure dissolve with methanol of 1 ~ 2 times of amount of crude product use weight ratio, carry out wash-out with pure methyl alcohol, sub-bottle is collected, and the 0.8-0.9 L partial concentration of wash-out effluent liquid is described aurones compounds.
3. aurones compounds preparation method according to claim 2, is characterized in that the described alcohol concn of B step is 70%, supersound extraction 3 times, each 6h.
4. aurones compounds preparation method according to claim 2 is characterized in that the described medicinal extract of C step is with the pure dissolve with methanol of 2 times of amounts of its weight ratio.
5. aurones compounds preparation method according to claim 2, is characterized in that the described medicinal extract of C step weighs 80 ~ 100 order silica gel mixed samples of 1 ~ 2 times with medicinal extract after dissolve with methanol.
6. aurones compounds preparation method according to claim 2, is characterized in that the described chloroform-methanol volume proportion of C step is 20:1,9:1,8:2,7:3,6:4,5:5.
7. aurones compounds preparation method according to claim 2, is characterized in that the described silicagel column of C step fills posts with 1 ~ 2 times of amount 200 ~ 300 purpose silica gel of medicinal extract weight.
8. aurones compounds preparation method according to claim 2, is characterized in that the described moving phase of D step is 48% methyl alcohol.
9. aurones compounds preparation method according to claim 2, is characterized in that the described crude product of the E step pure dissolve with methanol of 1.5 times of amounts of weight ratio.
10. the application of aurones compounds claimed in claim 1 in preparation resisting tobacco mosaic virus medicine.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103304530A (en) * | 2013-06-19 | 2013-09-18 | 云南烟草科学研究院 | Coumarin compound and preparation method and application thereof |
| CN105859668A (en) * | 2016-04-14 | 2016-08-17 | 云南中烟工业有限责任公司 | Benzofuran compound and preparation method thereof and application in preparation of drugs for resisting tobacco mosaic virus |
| US10899727B2 (en) | 2016-04-11 | 2021-01-26 | Middle Tennessee State University | Therapeutic aurones |
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| CN101002841A (en) * | 2006-12-27 | 2007-07-25 | 中国科学院新疆理化技术研究所 | Effective components of rose, its preparing method and use |
| CN101434592A (en) * | 2008-12-19 | 2009-05-20 | 沈阳药科大学 | Novel flavonoid extracted from Maackia amurensis |
| CN102827118A (en) * | 2012-09-08 | 2012-12-19 | 云南民族大学 | Siamaurone B compound and preparation method and application thereof |
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| CN101002841A (en) * | 2006-12-27 | 2007-07-25 | 中国科学院新疆理化技术研究所 | Effective components of rose, its preparing method and use |
| CN101434592A (en) * | 2008-12-19 | 2009-05-20 | 沈阳药科大学 | Novel flavonoid extracted from Maackia amurensis |
| CN102827118A (en) * | 2012-09-08 | 2012-12-19 | 云南民族大学 | Siamaurone B compound and preparation method and application thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103304530A (en) * | 2013-06-19 | 2013-09-18 | 云南烟草科学研究院 | Coumarin compound and preparation method and application thereof |
| CN103304530B (en) * | 2013-06-19 | 2014-08-27 | 云南烟草科学研究院 | Coumarin compound and preparation method and application thereof |
| US10899727B2 (en) | 2016-04-11 | 2021-01-26 | Middle Tennessee State University | Therapeutic aurones |
| US11286245B2 (en) | 2016-04-11 | 2022-03-29 | Middle Tennessee State University | Therapeutic aurones |
| CN105859668A (en) * | 2016-04-14 | 2016-08-17 | 云南中烟工业有限责任公司 | Benzofuran compound and preparation method thereof and application in preparation of drugs for resisting tobacco mosaic virus |
| CN105859668B (en) * | 2016-04-14 | 2018-03-09 | 云南中烟工业有限责任公司 | A kind of benzofuran compounds, its preparation method and the purposes in resisting tobacco mosaic virus medicine is prepared |
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| CN103113336B (en) | 2015-03-04 |
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